{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-07a7ddd270ed4ee294d08bcca20357f0","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"94fe2c698bb8e2e0dbd6544d44289ad99d1cfab188952202666819fc0a8ec184","doi":"10.1002/anie.201907366","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-14011173ac082dda","route_slugs":["ord-07a7ddd270ed4ee294d08bcca20357f0-bdd4fc431fe4"],"reactant_slugs":["ord-compound-34c6b1615e21656694e8"],"product_slugs":["ord-compound-e4d6cf1043511e28d483"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_830"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC=1C=CC=CC1)C2=CC=C(OC)C=C2"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7465-87-4"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.009,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=CC=CC2=C1NC(=C2C)C)C=3C=NC(=CC3)C4=NC=CC=C4"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2366213-69-4"}],"amount":{"moles":{"value":0.0198,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":3,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 1:1) as the eluent."},"outcomes":[{"reaction_time":{"value":96,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC=1C=CC=CC1)C2=CC=C(OC)C=C2B3OC(C)(C)C(O3)(C)C"},{"type":"CAS_NUMBER","value":"2366213-94-5"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":43}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (500 MHz, CDCl3) δ 8.35 (brs, 1H, amide-NH), 7.75 – 7.72 (m, 1H, Ha), 7.36 – 7.26 (m, 5H), 7.11 (s, 1H, Hc), 6.81 – 6.77 (m, 1H, Hb), 4.36 – 4.34 (m, 2H, Bn-CH2), 3.87 (s, 3H, OMe), 1.33 (s, 12H, pin-Me). 13C NMR (126 MHz, CDCl3) δ 170.86, 163.51, 137.07, 128.83, 128.27, 127.92, 126.75, 125.49, 115.33, 114.70, 82.03, 55.54, 45.06, 25.12."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 367.1956","data":{"found":{"float_value":367.1956,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201907366"}}},"entities":[{"slug":"ord-compound-34c6b1615e21656694e8","name":"C15H15NO2 · ORD GEFZSLMGZREDTO-UHFFFAOYSA-N","smiles":"COc1ccc(C(=O)NCc2ccccc2)cc1","inchi":"InChI=1S/C15H15NO2/c1-18-14-9-7-13(8-10-14)15(17)16-11-12-5-3-2-4-6-12/h2-10H,11H2,1H3,(H,16,17)","formula":"C15H15NO2"},{"slug":"ord-compound-e4d6cf1043511e28d483","name":"C21H26BNO4 · ORD QRPSPGOTSUZAMP-UHFFFAOYSA-N","smiles":"COc1ccc(C(=O)NCc2ccccc2)c(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C21H26BNO4/c1-20(2)21(3,4)27-22(26-20)18-13-16(25-5)11-12-17(18)19(24)23-14-15-9-7-6-8-10-15/h6-13H,14H2,1-5H3,(H,23,24)","formula":"C21H26BNO4"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-14011173ac082dda","title":"Literature experiment — 10.1002/anie.201907366","source_type":"paper","doi":"10.1002/anie.201907366","url":"https://doi.org/10.1002/anie.201907366","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}